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EP1086181B1 - Compositions de pigments monoazo laques, stables a la chaleur - Google Patents

Compositions de pigments monoazo laques, stables a la chaleur Download PDF

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Publication number
EP1086181B1
EP1086181B1 EP99924482A EP99924482A EP1086181B1 EP 1086181 B1 EP1086181 B1 EP 1086181B1 EP 99924482 A EP99924482 A EP 99924482A EP 99924482 A EP99924482 A EP 99924482A EP 1086181 B1 EP1086181 B1 EP 1086181B1
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Prior art keywords
composition
carbon atoms
group
group containing
methyl
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EP99924482A
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German (de)
English (en)
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EP1086181A1 (fr
Inventor
Amrit Pal Bindra
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BASF Catalysts LLC
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Engelhard Corp
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
    • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
    • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
    • C09B29/3647—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms
    • C09B29/3652—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles
    • C09B29/366—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a five-membered ring with two nitrogen atoms as heteroatoms containing a 1,2-diazoles or hydrogenated 1,2-diazoles containing hydroxy-1,2-diazoles, e.g. pyrazolone
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/0014—Monoazo dyes prepared by diazotising and coupling from diazotized aminonaphthalene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B63/00—Lakes
    • C09B63/005—Metal lakes of dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/41—Organic pigments; Organic dyes
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S534/00—Organic compounds -- part of the class 532-570 series
    • Y10S534/04—Azo compounds which are lakes

Definitions

  • This invention relates to novel laked azo pigments, processes for their preparation and to paint, plastic and ink compositions containing such pigments.
  • German Patent 2,616,981 describes metal salts of pyrazolone azo dyes which are obtained by coupling diazotized 2-amino-4, 5-dichlorobenzene-1-sulfonic acid with 1-(sulfoaryl)-3-methyl-5-pyrazolone compounds and subsequent laking with metal salts.
  • R is CH 3 or COO - ;
  • X is Cl, CH 3 , CH 3 O, C 2 H 5 O C 2 H 5 CONH, NH 2 CONH, C 6 H 5 CONH, CH 3 SO 2 NH, CH 3 CONH, or hydrogen;
  • Y is hydrogen, Cl, or CH 3 ;
  • Z is hydrogen or Cl, n is 0, 1 or 2;
  • Me + is one equivalent of a cation selected from the group consisting of NH 4 + , Li + , K + , Na + , 1/2 Sr 2+ , 1/2 Mn 2+ , 1/2 Ni 2+ , 1/2 Ba 2+ , 1/2 Mg 2+ and 1/2 Ca 2+; with the provision that if R is COO - , the additional equivalent charge is compensated by a further equivalent of said or another cation.
  • European Patent 0,126,405 (German Patent 33,180,373) also describes laked pyrazolone azo pigments of the formula wherein D is tri or tetrasubstituted phenyl ring; R is CH 3 or COO - ; X is Cl, Br, CH 3, CH 3 O, C 2 H 5 O CH 3 CONH, SO 2 NH 2 , SO 3 - ; Y is Cl, Br, CH 3 or SO 3 - ; Z is Cl, Br or CH 3 .
  • United States Patent 5,047,517 relates to a yellow monoazo pigment which is obtained by diazotization of 2-amino-4-chloro-5-methylbenzene-1-sulfonic acid, coupling of the diazonium compound with 1-(3'-sulfophenyl)-3-methyl-5-pyrazolone and subsequent laking of the coupling product to the calcium salt.
  • WO 96/25464 describes an azo yellow pigment comprising an aromatic amine coupled to a pyrazolone moiety.
  • a phenyl substituent on the pyrazolone moiety includes a substituent selected from a recited group which does not include a sulfonic acid group.
  • FR-A-2034686 describes a compound said to be suitable for dying natural and synthetic polyamide fibres, such as nylon, silk and wool, a pure light-fast lemon-yellow shade.
  • the compound has a methyl or chloro substituent on a phenyl moiety substituted on the pyrazolone group of an azo dye compound.
  • This invention relates to azo pigments for use as coloring agents and processes for their preparation.
  • a red shade yellow pigment composition comprising one or more compounds having the formula: wherein X is an alkyl group containing 1 to 4 carbon atoms or a -COOR 1 group; wherein R 1 is hydrogen or an alkyl group containing 1 to 4 carbon atoms; each Y is independently an alkyl group containing 1 to 4 carbon atoms, an alkyloxy group containing 1 to 4 carbon atoms, or halogen group; a is 0,1, or 2; and M is a divalent metal.
  • a process for preparing a red shade yellow pigment composition which comprises making an azo dye by:
  • this invention relates to paint, plastic and ink compositions containing the azo pigment compositions of this invention.
  • the pigments of the present invention may be prepared by initially diazotizing one or more aromatic amines wherein at least one of said amines is a 1-sulfo-2-naphthylamine; and thereafter coupling the diazonium component with a coupling component comprised of a pyrazolone coupler to form the desired dye.
  • the 1-sulfo-2-naphthylamines are characterized by the formula: and salts thereof.
  • Mixtures of two or more of any 1-sulfo-2-naphthylamines are within the scope of this invention. Also within the scope of this invention are mixtures of one or more 1-sulfo-2-naphthylamines and one or more second amines, other than 1-sulfo-2-naphthylamines, selected from aromatic amines containing at least one acid group and salts thereof. Such second amines can be useful for shade adjustments of the pigments of this invention.
  • Examples of preferred salts include ammonium and the alkali metal salts such as the sodium and potassium salts.
  • aromatic amines can be mixed with the 1-sulfo-2-naphthylamines for the purposes of the present invention.
  • Almost any primary aromatic amine can be used where the aromatic moiety of such amine contains at least one substituent acid group or salts thereof, preferably alkali metal or ammonium salts (Ar).
  • the aromatic amines may be monoamines or polyamines containing up to four or more amine groups per molecule.
  • the diazonium components derived from such amine may contain one diazonium group (mono-diazonium), two diazonium groups (bis-diazonium), three diazonium groups (tris-diazonium), etc.
  • the aromatic amines may be monocyclic amines such as aniline and its derivatives, or bicyclic amines such as naphthyl amine.
  • the aromatic amines may also be biphenylamines or polyamines such as aminobiphenyl, benzidine, and 3,3',4,4'-biphenyltetramine.
  • the aromatic amine is a primary aromatic amine characterized by the formula wherein each R is independently a halogen, hydrocarbyl, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group; n is 0, 1 or 2; each Z is independently a -COOH or -SO 3 H group, or salts of such groups; m is 1 or 2; wherein it is understood that the imidazalone group is represented by the formula -NH-C-NH- which, when taken together with the aromatic ring, the nitrogen atoms are bonded to adjacent carbons to form a five member ring.
  • hydrocarbyl as used in this specification and claims is intended to include hydrocarbons which may contain substituent groups such as ether, ester, nitro or halogen which do not materially affect the hydrocarbon character of the group.
  • the aromatic amines characterized by Formula I may contain 0, 1 or 2 R groups which are each independently a halogen, hydrocarbyl, hydrocarbyloxy, carboxylic acid ester, sulfonic acid ester, carboxylic acid amide, imidazolone, sulfonic acid amide or nitro group.
  • the halogen group can be any of the halogens, although chlorine and bromine are generally used, with chlorine being the most preferred example of a halogen substituent.
  • the hydrocarbyl groups may independently be alkyl, cycloalkyl, aryl, aralkyl or alkaryl groups. For example, if R is an unsubstituted aryl group, the aromatic amine is a biphenyl amine.
  • R When R is an alkyl group, the alkyl group will contain from one to four carbon atoms.
  • R is a hydrocarbyloxy group
  • the hydrocarbyl moiety may be any of the hydrocarbyl groups discussed above although the hydrocarbyloxy group is an alkoxy group containing from 1 to 4 carbon atoms.
  • Preferred R groups are methyl, ethyl and chloro groups.
  • the aromatic amines characterized by Formula I also contain one or two acid groups of -COOH and -SO 3 H, or salts thereof. In one embodiment, the aromatic amine of Formula I contains an -SO 3 H group.
  • Examples of aromatic amines characterized by Formula I wherein Z is a sulfonic acid group and m is 1 include 2-aminobenzene-1-sulfonic acid, 4-aminobenzene-1-sulfonic acid, 2-amino-5-methylbenzene-1-sulfonic acid, 2-amino-5-methoxybenzene-1-sulfonic acid, 3-amino-6-methylbenzene-1- sulfonic acid, 2-amino-4-chloro-5-methylbenzene-1-sulfonic acid, 2-amino-5-chloro-4-ethylbenzene-1-sulfonic acid, 2-amino-5-chloro-4-methylbenzene-1-sulfonic acid, etc.
  • Examples of aromatic amines characterized by Formula I wherein Z is a carboxylic acid group, and m is 1 include 2-aminobenzoic acid, 3-aminobenzoic acid, 4-aminobenzoic acid, 2-amino-5-methylbenzoic acid, 2-amino-6-methylbenzoic acid, 3-amino-2-methylbenzoic acid, 2-amino-3-methoxybenzoic acid, 4-amino-3-methoxybenzoic acid, 4-amino-5-chloro-2-methoxybenzoic acid, 2-amino-4-chlorobenzoic acid, 3-amino-4-chlorobenzoic acid, etc.
  • the benzene sulfonic acid and benzoic acid compounds can be used per se or as their salts. Examples of preferred salts include the alkali metal salts such as the sodium and potassium salts.
  • aromatic amines from which the diazonium components are prepared may be fused cyclic aromatic amine compounds such as compounds derived from various naphthalenes other than 1-sulfo-2-naphthylamines including, 4-aminonaphthalene-1-sulfonic acid, etc.
  • aromatic amines which are biphenyl amines and polyamines include 4-aminobiphenyl-3'- sulfonic acid, and 4,4'-diaminobiphenyl-2,2'-disulfonic acid.
  • the diazotization of the amines useful for the purposes of this invention may be carried out in the manners known to those skilled in the art through the use of alkali metal nitrites or lower alkyl nitrites together with an adequately strong acid such as a mineral acid.
  • useful mineral acid include hydrochloric acid and sulfuric acid. Nitrosyl sulfuric acid also can be utilized.
  • the diazotization reaction can be conducted at a temperature in the range of from about -20 to +30°C, preferably from 0 to 20°C.
  • a surface-active agent such as a non-ionic, anionic or cationic surface active agent and, optionally, appropriate organic solvents such as, for example, glacial acetic acid, lower alkanols, dioxane, formamide, dimethyl formamide, dimethyl sulfoxide, pyridine or N-methyl pyrrolidone.
  • pyrazolone couplers useful for the purposes of this invention are represented by the formula: and salts thereof; wherein X is a lower alkyl or a -COOR 1 group; wherein R 1 is hydrogen or lower alkyl group; each Y is independently a lower alkyl, lower alkyloxy or halogen group; a is 0,1, or 2.
  • the pyrazolone couplers useful for the purposes of this invention are characterized by the formula: wherein X is a methyl, ethyl, --COOH, --COOCH 3 , --COOCH 2 CH 3 , more preferably,
  • the coupling reaction useful for the purposes of the present invention may be effected preferably by adding the diazonium components to coupling components, but the coupling components can be added to the diazonium components. Coupling is generally effected at a temperature of from about -20 to about 80°C, preferably from about 20 to about 65°C. As in a diazotization reaction, coupling may be carried out in the presence of an appropriate surface active agent or organic solvent, such as all of those identified above for the diazotization reaction.
  • the coupling component is dissolved in a basic solution such as an aqueous alkali metal hydroxide solution and reprecipitated with a dilute acid such as acetic acid.
  • a basic solution such as an aqueous alkali metal hydroxide solution
  • a dilute acid such as acetic acid
  • the diazonium component is coupled with a slight stoichiometric excess of the coupling component. That is, one equivalent of the diazonium component is coupled with slightly more than one equivalent of the coupling component.
  • the dispersibility of the pigments of the present invention can be improved by adding alkali-soluble resin-like products before, during, or after the coupling is completed or after the metallization discussed below.
  • resin-like materials can be added for this purpose, and these include for example, rosin resins, polymeric rosins, resin soap, chemically modified rosin resins such as rosin-maleinate resins, alkyd resins, and other synthetic hydrocarbon resins with a higher acid number, or combination of these resins.
  • the resins may be present in a product with free carboxyl groups that are capable of forming a salt, or may be partially or completely in the form of salts, for example, with alkali metal ions. It may also be advantageous to perform the coupling reaction in the presence of a finely divided insoluble material, for example, alkaline earth metal sulphates and carbonates, titanium dioxide or clay materials or very finely divided organic plastic materials.
  • the composition prepared by the above-described coupling reaction can be metallized by a divalent metal salt which forms the sulfonate salt. This is also known as laking and forms the azo pigment.
  • the metal salt may be a salt of alkaline earth metals, manganese, nickel or zinc or mixtures of two or more of these metals. Alkaline earth metal salts are preferred. Alkaline earth metal salts such as SrCl 2 and CaCl 2 are particularly useful for this purpose.
  • Metallization may be accomplished preferably by adding the metal salt to the dye after coupling all of the diazonium component present is complete or, by including the metal salt in the diazonium component whereby metallization occurs as the dye is formed.
  • the product of the metallization may be heated to reflux temperature for about 1 to 3 hours or at temperatures above 100°C under pressure in the presence of the above-described resin soaps or other soluble resins.
  • the azo pigments are recovered from the water-based reaction slurry by filtering to form a presscake of pigment which is washed with hot (e.g., 40-60°C) water so as to remove the excess acids, bases and salts formed in the coupling reaction.
  • the presscake is typically washed with from about 10 to 20 times its volume of hot water.
  • the filter cake is generally washed until the filtrate gives only a slightly positive test for chloride ion.
  • the washed presscakes can be dried, ground and used in the form of a coarse or finely divided powder.
  • the azo pigments of this invention can be dispersed into oleoresinous vehicles to prepare flushed bases or dispersed into aqueous vehicles to prepare aqueous dispersions.
  • the pigment compositions of this invention provide red shade yellow pigments having improved color strength, resistance to polar solvent, light fastness and/or heat stability and are useful as coloring agents in plastics, paints and inks.
  • This invention also relates to paint, ink and plastic compositions comprising major amounts of a paint vehicle, ink vehicle or plastic and minor amounts of the compositions of this invention.
  • inks include printing inks and lacquers
  • plastics include thermoplastic and thermosetting materials, natural resins and synthetic resins, polystyrene and its mixed polymers, polyolefins, in particular polyethylene and polypropylene, polyacrylic compounds, polyvinyl compounds, for example polyvinyl chloride and polyvinyl acetate, polyesters and rubber, and also filaments made of viscose and cellulose ethers, cellulose esters, polyamides, polyurethanes, polyesters, for example polyglycol terephthalates, and polyacrylonitrile. It is also useful for pigment printing and for the pigmenting of paper in the mass.
  • the pigment is in particular suitable for the pigmenting of plastics in the mass, such as, for example, of polystyrene and its mixed polymers, polyolefins, in particular polyethylene and polypropylene and the corresponding mixed polymers, polyvinyl chloride and polyesters in particular polyethylene glycol terephthalate and polybutylene terephthalate and the corresponding mixed condensation products based on polyesters.
  • plastics in the mass such as, for example, of polystyrene and its mixed polymers, polyolefins, in particular polyethylene and polypropylene and the corresponding mixed polymers, polyvinyl chloride and polyesters in particular polyethylene glycol terephthalate and polybutylene terephthalate and the corresponding mixed condensation products based on polyesters.
  • plastics in the mass such as, for example, of polystyrene and its mixed polymers, polyolefins, in particular polyethylene and polypropylene and the corresponding mixed polymers, polyvinyl chloride and polyester
  • compositions of the present invention and their methods of preparation. Unless otherwise indicated in the following examples and elsewhere in the specification and claims, all parts and percentages are by weight, temperatures are in degrees centigrade and pressures are at or near atmospheric.
  • 2-aminonaphthalene-1-sulfonic acid (13.1 parts) are dissolved in 300 parts of water and 2.5 parts of sodium hydroxide by stirring at 40-45°C.
  • the solution is cooled to 0°C by the addition of ice and diazotized by the addition of 4 parts sodium nitrite in 12 parts of water followed by addition of 17.5 parts 20 Baume hydrochloric acid and stirring the solution at 0-10°C for 30 minutes. Excess nitrous acid is then quenched by the addition of sulfamic acid.
  • the slurry is chilled to 0°C by addition of ice.
  • a solution of 6 parts of calcium chloride dihydrate in 14 of water is then added to the slurry.
  • the sodium salt of 1-naphthylamine-4-sulfonic acid (8.9 parts) and 100 parts of water are stirred together with the addition of sufficient 50% sodium hydroxide solution to form a solution alkaline to Brilliant Yellow paper.
  • the solution is placed in an ice bath and cooled to 0-5°C and 15 parts of 20 Baume hydrochloric acid are added.
  • a solution of 3.13 parts of sodium nitrite in 9.4 parts of water is added and the mixture is stirred at 0-5°C for 30 minutes. Excess nitrous acid is then quenched by the addition of sulfamic acid.
  • the slurry is chilled to 0°C by addition of ice.
  • Dissolved in 200 parts of water are 13.2 parts of 1-(3'-sulfophenyl)-3-methyl-5-pyrazolone and 2.5 parts of sodium hydroxide, The temperature of this solution is adjusted to 5°C. pH is adjusted to 6.5 and the diazonium slurry is then slowly added to it while maintaining the pH at 6-7 through the addition of sodium hydroxide. The pH of the slurry is adjusted to 6.5 and the mixture is stirred overnight at room temperature. The reaction mixture is then heated to 90°C and a solution of 48 parts of calcium chloride dihydrate in 112 parts of water is added. The mixture is then stirred further for a 3 hours at 90°C, cooled to 55°C and filtered. The filtercake is washed with water, dried overnight at 70°C and pulverized to give an orange pigment powder.
  • Example 1 The procedure of Example 1 is repeated, except that instead of the addition of calcium chloride, 5.7 parts of strontium nitrate in 17.5 parts of water are added to the diazonium slurry and 21 parts of strontium nitrate in 49 parts of water are added after coupling instead of the addition of calcium chloride. A yellowish orange pigment powder is obtained.
  • Comparative Example 1 The procedure of Comparative Example 1 is repeated, except that instead of the addition of calcium chloride, 48 parts of strontium nitrate in 112 parts of water are added. An orange pigment powder is obtained.
  • Comparative Example 1A The procedure of Comparative Example 1A is repeated, except that instead of the addition of calcium chloride, 48 parts of strontium nitrate in 112 parts of water are added. An orange pigment powder is obtained.
  • Example 1 The procedure of Example 1 is repeated, except that instead of the addition of calcium chloride, 8 parts of manganese sulfate hydrate are added to the diazonium slurry and 18 parts of manganese sulfate hydrate are added after coupling instead of the addition of calcium chloride. A yellowish orange pigment powder is obtained.
  • a mixture of 0.5 part pigment, 0.5 part titanium dioxide (DuPont Ti-Pure R - 960) and 500 parts high density polyethylene (Solvay T50-2000-G) is shaken on a paint shaker to uniformity, then injection molded at 232°C in a 30 ton Battenfield machine.
  • Spectrophotometric values are measured with a Macbeth Color-Eye (specular component included, large area) to give the apparent strength and hue angle under Illuminant D, 10°, shown in the Table I.
  • the pigments obtained according to the present invention display strong, bright reddish shade yellows in contrast to the weak orange to reddish orange shades displayed by pigments derived from 1-naphthylamine-4-sulfonic acid and 1-naphthylamine-6-sulfonic acid.
  • the calcium salt of the dye obtained by coupling diazotized 2-amino naphthalene- 1-sulfonic acid with 1-(3'-sulfophenyl)-3-methyl-5-pyrazolone (Example 1) displays a strong, bright reddish yellow color (hue angle 66.3).
  • the high chromaticity value (73.0) is consistent with the brightness of the color displayed while the high strength is reflected by a high K/S value of 23.1.
  • the corresponding pigment obtained by using 1-naphthylamine-4-sulfonic acid in place of 2-aminonaphthalene-1-sulfonic acid shows a very weak and dull reddish orange color (hue angle 45.4) of low chromaticity (32.4) and very low strength (K/S value of only 4.9).
  • the corresponding pigment obtained by using 1-naphthylamine-6-sulfonic acid also displays a weak orange color (hue angle 59.7) of low chromaticity (52.6) and low strength (K/S value of 17.8).
  • the strontium salt of the dye obtained by coupling diazotized 2-amino naphthalene-1-sulfonic acid with 1-(3'-sulfophenyl)-3-methyl-5-pyrazolone (Example 2) displays a strong, bright reddish yellow color (hue angle 70.3).
  • the high chromaticity value (78.2) is consistent with the brightness of the color displayed and the high strength is reflected by a high K/S value of 26.8.
  • the corresponding pigment obtained by using 1-naphthylamine-4-sulfonic acid in place of 2-aminonaphthalene-1-sulfonic acid shows a very weak and dull reddish orange color (hue angle 43.7) of low chromaticity (37.6) and very low strength (K/S value of only 6.3).
  • the pigment obtained by using 1-naphthylamine-6-sulfonic acid displays a weak orange color (hue angle 49.9) of low chromaticity (60.4) and relatively low strength (K/s value of 20.3).

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
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  • Paints Or Removers (AREA)
  • Cosmetics (AREA)

Claims (22)

  1. Composition de pigment jaune à nuance rouge comprenant un ou plusieurs composés ayant la formule :
    Figure 00250001
    dans laquelle :
    X est un groupe alkyle contenant 1 à 4 atomes de carbone ou un groupe -COOR1; dans lequel R1 est un atome d'hydrogène ou un groupe alkyle contenant 1 à 4 atomes de carbone ;
    chaque Y est indépendamment un groupe alkyle contenant 1 à 4 atomes de carbone, un groupe alkyloxy contenant 1 à 4 atomes de carbone ou un atome d'halogène ;
    a est 0, 1 ou 2 ; et
    M est un métal divalent.
  2. Composition selon la revendication 1 dans laquelle X est un groupe méthyle ou éthyle.
  3. Composition selon la revendication 1 dans laquelle chaque Y est indépendamment un groupe méthyle ou chloro ; et a est 0 ou 1.
  4. Composition selon la revendication 3 dans laquelle X est un groupe méthyle et a est 0.
  5. Composition selon la revendication 1 dans laquelle M est un métal alcalino-terreux, le manganèse, le nickel ou le zinc.
  6. Composition selon la revendication 4 dans laquelle M est le calcium, le strontium, le baryum ou des mélanges de ceux-ci.
  7. Composition de pigment jaune à nuance rouge selon la revendication 1 comprenant un ou plusieurs composés ayant la formule :
    Figure 00260001
    dans laquelle X est un groupe alkyle contenant 1 à 4 atomes de carbone ; et M est un métal divalent.
  8. Composition selon la revendication 7 dans laquelle M est un métal divalent choisi dans le groupe constitué des métaux alcalino-terreux, du manganèse, du nickel et du zinc.
  9. Composition selon la revendication 7 dans laquelle X est un groupe méthyle ou éthyle.
  10. Composition selon la revendication 7 dans laquelle M est le calcium, le strontium, le baryum ou des mélanges de ceux-ci.
  11. Procédé de préparation de composition de pigment jaune à nuance rouge qui comprend la fabrication d'un colorant azoïque par :
    copulation (i) d'un composant diazonium comprenant une ou plusieurs amines aromatiques dans lesquelles au moins une desdites amines est une 1-sulfo-2-naphtylamine ayant la formule :
    Figure 00270001
    et les sels de celle-ci ;
    avec (ii) un composant de copulation ayant la formule :
    Figure 00270002
    et les sels de celui-ci ;
    formule dans laquelle :
    X est un groupe alkyle contenant 1 à 4 atomes de carbone ou un groupe -COOR1; dans lequel R1 est un atome d'hydrogène ou un groupe alkyle contenant 1 à 4 atomes de carbone ;
    chaque Y est indépendamment un groupe alkyle contenant 1 à 4 atomes de carbone, un groupe alkyloxy contenant 1 à 4 atomes de carbone ou un atome d'halogène ;
    a est 0, 1 ou 2 ;
    et en métallisant ledit colorant avec au moins un métal divalent.
  12. Procédé selon la revendication 11 dans lequel X est un groupe méthyle ou éthyle.
  13. Procédé selon la revendication 11 dans lequel chaque Y est indépendamment un groupe méthyle ou chloro ; et a est 0, ou 1.
  14. Procédé selon la revendication 13 dans lequel X est un groupe méthyle et a est 0.
  15. Procédé selon la revendication 11 dans lequel M est un métal alcalino-terreux, le manganèse, le nickel ou le zinc.
  16. Procédé selon la revendication 15 dans lequel M est le calcium, le strontium, le baryum ou des mélanges de ceux-ci.
  17. Composition de peinture comprenant une quantité principale d'un véhicule de peinture et une quantité mineure de la composition selon la revendication 1.
  18. Composition de peinture comprenant une quantité principale d'un véhicule de peinture et une quantité mineure de la composition préparée selon le procédé de la revendication 11.
  19. Composition d'encre comprenant une quantité principale d'un véhicule d'encre et une quantité mineure de la composition selon la revendication 1.
  20. Composition d'encre comprenant une quantité principale d'un véhicule d'encre et une quantité mineure de la composition préparée selon le procédé de la revendication 11.
  21. Composition de plastique comprenant une quantité principale d'une matière plastique et une quantité mineure de la composition selon de la revendication 1.
  22. Composition de plastique comprenant une quantité principale d'une matière plastique et une quantité mineure de la composition préparée par un procédé selon la revendication 11.
EP99924482A 1998-06-08 1999-05-24 Compositions de pigments monoazo laques, stables a la chaleur Expired - Lifetime EP1086181B1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US93317 1987-09-04
US09/093,317 US5997628A (en) 1998-06-08 1998-06-08 Heat stable laked monoazo pigment compositions
PCT/US1999/011462 WO1999064521A1 (fr) 1998-06-08 1999-05-24 Compositions de pigments monoazo laques, stables a la chaleur

Publications (2)

Publication Number Publication Date
EP1086181A1 EP1086181A1 (fr) 2001-03-28
EP1086181B1 true EP1086181B1 (fr) 2003-05-02

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Country Status (8)

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US (1) US5997628A (fr)
EP (1) EP1086181B1 (fr)
CN (1) CN1111191C (fr)
AT (1) ATE239060T1 (fr)
AU (1) AU4096899A (fr)
CA (1) CA2334512C (fr)
DE (1) DE69907449T2 (fr)
WO (1) WO1999064521A1 (fr)

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US6235100B1 (en) * 1999-06-24 2001-05-22 Engelhard Corporation Metallized azo yellow pigments
US6294012B1 (en) * 1999-11-15 2001-09-25 Engelhard Corporation High strength monoazo yellow pigment
US6387170B1 (en) * 2000-08-28 2002-05-14 Dominion Colour Corporation Heat stable orange laked monoazo pigment
BR0114017A (pt) * 2000-09-21 2003-07-22 Ciba Sc Holding Ag Composição de pigmento azo laranja
IL150317A0 (en) * 2002-06-19 2002-12-01 Yissum Res Dev Co Organo-clay complexes
CN100390241C (zh) * 2002-08-26 2008-05-28 富士胶片株式会社 喷墨记录油墨和喷墨记录方法
US7141104B2 (en) * 2003-06-05 2006-11-28 Agfa-Gevaert UV-absorbing ink composition for ink-jet printing
EP1484368B1 (fr) * 2003-06-05 2006-01-11 Agfa-Gevaert Composition d'encre absorbant la lumière ultraviolette pour l'enregistrement par jet d'encre
US20070022907A1 (en) * 2004-11-23 2007-02-01 Basf Catalysts Llc Colored Masterbatch Precursor
US7473310B2 (en) * 2007-06-07 2009-01-06 Xerox Corporation Nanosized particles of monoazo laked pigment and non-aqueous compositions containing same
US7470320B1 (en) * 2007-06-07 2008-12-30 Xerox Corporation Nanosized particles of monoazo laked pigment with tunable properties
US7465348B1 (en) * 2007-06-07 2008-12-16 Xerox Corporation Nanosized particles of monoazo laked pigment
US7465349B1 (en) * 2007-06-07 2008-12-16 Xerox Corporation Method of making nanosized particles of monoazo laked pigment
CN101376748B (zh) * 2007-08-27 2011-09-14 明德国际仓储贸易(上海)有限公司 黄色染料化合物及其之墨水组成物
CN101245195B (zh) * 2008-03-14 2010-06-09 上海富圆染化有限公司 一种杂环偶氮阳离子染料及其制备方法
JP5623154B2 (ja) * 2009-07-10 2014-11-12 日東電工株式会社 液晶性コーティング液および偏光膜
CN107353669B (zh) * 2017-06-30 2018-11-06 深圳市国华光电科技有限公司 一种黄色染料、油墨和电润湿显示器
US20230312948A1 (en) * 2020-06-28 2023-10-05 Dic Corporation Pigment composition, printing ink, and method for manufacturing pigment composition

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Also Published As

Publication number Publication date
ATE239060T1 (de) 2003-05-15
US5997628A (en) 1999-12-07
EP1086181A1 (fr) 2001-03-28
CA2334512A1 (fr) 1999-12-16
DE69907449T2 (de) 2004-04-08
CA2334512C (fr) 2008-07-29
CN1308655A (zh) 2001-08-15
WO1999064521A1 (fr) 1999-12-16
AU4096899A (en) 1999-12-30
DE69907449D1 (de) 2003-06-05
CN1111191C (zh) 2003-06-11

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